Synthesis and photolysis of doxyl derivatives of 5β‐androstan‐3‐ones

In an unsuccessful attempt to effect remote functionalization at C9, 4,4‐dimethyloxazolidine‐ N ‐oxyl (doxyl) derivatives at C3 of 5β‐androstan‐3,17‐dione and 5β‐androstan‐17β‐ol‐3‐one were prepared and photolyzed. The former doxyl yielded its C13 stereoisomer; the latter was converted very slowly to intractable material.